I think there is advice I have that I can provide to the first thing you describe there. The scale of achievement is not a linear thing. A lot of people say they feel left behind by the progress of others, such as them having kids, getting high ranking jobs, finding homes, and so on, but it's often idealized. Some of those things are double-edged swords (for example some might give you their kids in an instant, as blunt as that sounds), or they might have something that brings them back in this progress.

There was a girl in my friend's high school class that those who felt left behind would always compare themselves to. She was going up and up in progress but married and once married it just spiraled out of control until she ended up giving all her progress up. She's currently living with a friend and she's not looking high-spirited to say the least. Another got taken advantage of in his quest for progress and entered a cult who wanted a high ranking new voice, and his life just got wobbly. Another is in jail/prison. Another just got out of prison and has nothing. Sometimes it is better to adapt to level one.